Executive Assistant

We are a short-term rental management company based on Boston’s North Shore in Massachusetts. We manage around 45 vacation rental properties for homeowners and a 10-unit boutique hotel. We are a fast-moving, high quality, family-run business.

About the Role

You will be the right hand to our COO, Rachel. She runs day-to-day operations across all of our businesses and needs someone who can take work off her plate, keep her organized, and make sure nothing falls through the cracks. A large part of this role is handling payments, payroll, and bookkeeping, so accuracy matters. This is not a task-taker role. We want someone who notices what needs to be done, follows up without being reminded, and gets better at anticipating Rachel’s needs every week.

Schedule: Starting at Part-time, 25 hours per week, Monday to Friday, US Eastern Time business hours (some flexibility)
Pay: $5.00
Start date: as soon as possible

What You’ll Do

Finance and payments

Review and pay vendor invoices, including our cleaning team
Process payouts to all vendors, including field inspectors and handymen
Run payroll for our boutique hotel
Run the monthly tips report from our guest messaging platform and make sure tips are distributed correctly
Confirm rent has been received on our long-term rental properties and follow up on anything late
Review and categorize monthly expenses for our long-term rental properties in Stessa
Pay non-automated long-term rental expenses such as property taxes and utilities
Process monthly owner statements for our property owners
File monthly Massachusetts room occupancy tax submissions through MassTaxConnect
Categorize transactions and reconcile accounts in QuickBooks
Track receipts, invoices, and bills, and flag anything overdue or unusual

Executive support

Manage Rachel’s email inbox: sort, flag priorities, draft replies, and follow up on open threads
Manage her calendar: schedule meetings, send invites, confirm appointments, and protect focus time
Keep a running task list for Rachel and follow up with team members on deadlines
Take notes in meetings and send out action items afterward
Prepare documents, reports, and summaries she needs for meetings
Handle personal admin tasks as needed (appointments, bookings, errands that can be done online)

Operations support

Track open items across the team in Slack and make sure they get resolved
Coordinate with our virtual assistant team, cleaners, and maintenance vendors when Rachel needs something chased down
Help maintain SOPs, checklists, and training documents
Support owner communication: draft updates, gather information, and keep records organized

What We’re Looking For

2+ years of experience as an executive assistant, personal assistant, or virtual assistant for a business owner or executive
Bookkeeping or accounts payable experience (QuickBooks Online strongly preferred)
Experience running payroll
Comfortable handling payments and financial data accurately and confidentially
Excellent written and spoken English
Very organized and detail-oriented. You don’t let things slip.
Proactive. You ask questions, raise problems early, and suggest better ways to do things.
Comfortable learning new software quickly
Reliable internet, a quiet workspace, and a backup power source
Able to work US Eastern Time hours

Nice to Have

Experience with Stessa or other rental property accounting software
Experience in short-term rentals, vacation rentals, hospitality, or property management
Familiarity with Google Workspace, Slack, Hospitable, or similar tools

What We Offer

Long-term, stable full-time position
Direct work with leadership in a growing company
Room to grow as the business expands
Paid time off after commiserate with tenure

How to Apply

Please read this carefully. Applications that don’t follow these instructions will not be considered.

Use the subject line: “EA for Rachel: [Your Name]”
Tell us in a few sentences about a time you made a busy executive’s life easier without being asked
List the tools and software you are comfortable using
Tell us about your bookkeeping and payroll experience and which software you used
Include a link to a short (2 minute max) video introducing yourself

Email ---------- with the above application.